Ammonium formate → 4-Amino-4-methyl-cyclohexanol

HRID 855855Notes

Reaction equation

HRID 855855 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)(C)C>[NH2:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66756996benzyl N-(4-hydroxy-1-methylcyclohexyl)carbamate

Product 1

HCID 223798474-Amino-4-methyl-cyclohexanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of example 45E (169 mg, 0.64 mmol), ammonium formate (105 mg, 1.67 mmol) and 10% palladium on carbon (7 mg) in isopropanol (5 mL) was heated at 80° C. for 1 hour. The reaction mixture was cooled and filtered through a plug of Celite. The filter pad was washed with ethyl acetate (50 mL), and the filtrate was concentrated in vacuo to afford the titled compound as an inseparable mixture of diastereomers. MS (CI) m/z 130 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 3.77-3.71 (m, 2H), 3.65-3.61 (m, 2H), 1.87-1.61 (m, 4H), 1.63-1.33 (m, 10H), 1.15 (s, 3H), 1.11 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a plug of Celite
  3. washThe filter pad was washed with ethyl acetate (50 mL)
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2bc7c2f79903429da4ba2a95cda9236c
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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